N-Substituted 2-Aminobiphenylpalladium Methanesulfonate Precatalysts and Their Use in C–C and C–N Cross-Couplings | Zendy

Nicholas C. Bruno | Zendy; Nootaree Niljianskul | Zendy; Stephen L. Buchwald | Zendy

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N-Substituted 2-Aminobiphenylpalladium Methanesulfonate Precatalysts and Their Use in C–C and C–N Cross-Couplings

Author(s) -

Nicholas C. Bruno,

Nootaree Niljianskul,

Stephen L. Buchwald

Publication year - 2014

Publication title -

the journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.2

H-Index - 228

eISSN - 1520-6904

pISSN - 0022-3263

DOI - 10.1021/jo500355k

Subject(s) - chemistry , phosphine , palladium , catalysis , nitrogen , medicinal chemistry , polymer chemistry , coupling reaction , organic chemistry , combinatorial chemistry

A series of phosphine-ligated palladium precatalysts based on N-methyl- and N-phenyl-2-aminobiphenyl have been developed. Substitution at the nitrogen center prevents the presence of traces of aminobiphenyls that contain a free -NH2 group from contaminating cross-coupling products. These precatalysts produce N-substituted carbazoles upon activation, which cannot consume starting materials. These precatalysts were efficiently generated from 2-aminobiphenyl with minimal purification and found to be highly effective in Suzuki-Miyaura and C-N cross-coupling reactions.

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